SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE

被引：26

作者：

ALONSO, I ^{[1
]}

CID, MB ^{[1
]}

CARRETERO, JC ^{[1
]}

RUANO, JLG ^{[1
]}

HOYOS, MA ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID CANTO BLANCO,DEPT QUIM C-I,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)80020-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure 2-p-tolylsulfinylmaleates 1, 2 and 3 have been readily prepared by Knoevenagel reaction between (S)-menthyl p-toluenesulfinate and glyoxylic acid. Their asymmetric Diels-Alder reactions with cyclopentadiene have been studied under a wide range of uncatalyzed and catalyzed conditions and the stereochemical results have been explained by assuming a steric control approach, in term of S-cis or S-trans favoured conformations. Uncatalyzed Diels-Alder reactions of 1 and some Lewis acid catalyzed Diels-Alder reactions of 2 show high facial and endo selectivities. The facial selectivity of dienophile 2 highly depends on the Lewis acid, whereas reactivity of 1 and 3 is very sensitive to the solvent. These sulfinylmaleates 1, 2 and 3 act as synthetic equivalents of chiral acetylenedicarboxylates in Diels-Alder reactions after basic elimination of the sulfinylic moiety in the resulting adducts.

引用

页码：1193 / 1207

页数：15

共 32 条

[1] HIGHLY DIASTEREOSELECTIVE DIELS-ALDER REACTION OF OPTICALLY-ACTIVE 2-PARA-TOLYLSULPHINYL-2-CYCLOALKENONES WITH CYCLOPENTADIENE
ALONSO, I
CARRETERO, JC
RUANO, JLG
[J]. TETRAHEDRON LETTERS, 1989, 30 (29) : 3853 - 3856
[2] SYNTHESIS AND DIELS-ALDER REACTIONS OF TERT-BUTYL AND TERT-BUTYL, METHYL (S)S-2-PARA-TOLYLSULFINYLMALEATES, CHIRAL SYNTHETIC EQUIVALENTS OF MONOALKYL AND MIXED DIALKYL ACETYLENEDICARBOXYLATES
ALONSO, I
CARRETERO, JC
RUANO, JLG
[J]. TETRAHEDRON LETTERS, 1991, 32 (07) : 947 - 950
[3] DIMETHYL (R)S-2-(10-ISOBORNYLSULFINYL)MALEATE, A CHIRAL SYNTHETIC EQUIVALENT OF DIMETHYL ACETYLENEDICARBOXYLATE - PREPARATION AND ITS APPLICATION TO THE FORMAL CHIRAL SYNTHESIS OF (-)-NEPLANOCIN A AND (-)-ARISTEROMYCIN
ARAI, Y
HAYASHI, K
KOIZUMI, T
SHIRO, M
KURIYAMA, K
[J]. TETRAHEDRON LETTERS, 1988, 29 (47) : 6143 - 6146
[4] OPTICALLY-ACTIVE 2-PARA-TOLYLSULFINYLACRYLATE - A NOVEL CHIRAL DIENOPHILE WHICH EXHIBITS HIGH REACTIVITY AND DIASTEREOSELECTIVITY
ARAI, Y
KUWAYAMA, S
TAKEUCHI, Y
KOIZUMI, T
[J]. TETRAHEDRON LETTERS, 1985, 26 (50) : 6205 - 6208
[5] POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES
ARAI, Y
MATSUI, M
KOIZUMI, T
SHIRO, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 1983 - 1985
[6] ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH
ARITA, M
ADACHI, K
ITO, Y
SAWAI, H
OHNO, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) : 4049 - 4055
[7] DIENOPHILICITY OF CAPTODATIVE OLEFINS .6. SYNTHESIS AND DIELS-ADLER CYCLO-ADDITION REACTIONS OF ALPHA-ALKYLTHIO ALKYL ACRYLATES WITH CYCLOPENTADIENE - INFLUENCE OF STERIC FACTORS ON REACTIVITY AND STEREOSELECTIVITY
BOUCHER, JL
STELLA, L
[J]. TETRAHEDRON, 1988, 44 (12) : 3595 - 3605
[8] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES
CARRENO, MC
RUANO, JLG
MARTIN, AM
PEDREGAL, C
RODRIGUEZ, JH
RUBIO, A
SANCHEZ, J
SOLLADIE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) : 2120 - 2128
[9] STEREOSPECIFIC TOTAL SYNTHESIS OF DL-PENTALENOLACTONE
DANISHEFSKY, S
HIRAMA, M
GOMBATZ, K
HARAYAMA, T
BERMAN, E
SCHUDA, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) : 6536 - 6538
[10] SELF-INDUCED DIASTEREOSELECTIVE OXIDATION OF VINYL SULFIDES BEARING A CHIRAL HYDROXY GROUP AS A WAY OF PREPARATION OF OPTICALLY-ACTIVE SULFINYL DIENOPHILES AND THEIR USE IN THE ASYMMETRIC DIELS-ALDER REACTION TO CYCLOPENTADIENE
DELUCCHI, O
LUCCHINI, V
MARCHIORO, C
VALLE, G
MODENA, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) : 1457 - 1466

← 1 2 3 4 →